April 12 - 20, 2026
Spring 2026: Wine, Chocolate & You in Sicily
Bella Sicilia is calling…
Close your eyes and imagine the golden glow of the Italian sunset, painting the hills with hues of orange and pink. You are lounging in luxury, sipping on a glass of velvety wine and soaking in the beauty of the moment.
But this trip is more than just relaxation—it's an adventure off the beaten path, whisking you away from bustling metropolises and into the heart of authentic Sicilian charm.
Make Your Dream Come True
LOW $500 Deposit to Secure Your Spot
Starting at
$8,795 USD
Per Person
Double Occupancy
Starting at
$9,295 USD
Per Person
Single Occupancy
Book more than one trip and save $500!
Bring a friend and save $250!
September 1, 2025 - $3,995 payment is due
November 1, 2025 - the balance is due
The Trip at a Glance
Day 1 (Apr 12 - starting at 6 pm)
Welcome to Italy! Rest + get ready for the group welcome dinner
Day 2
• 9:45am - departure
• Start your cultural and culinary immersion in Palermo
• 1:30pm - back to hotel
• Group dinner
Day 3
• 7:45am - departure
• History & culture in central Sicily; Roman villa, artisanal crafts, Staircase of Santa Maria del Monte
• 5pm - check-in at the hotel
Day 4
• 8:45am - departure
• Ortigia city & food tour; taste Sicilian appetizers, local wines & a granita
• 2:30pm - back to hotel for an afternoon at leisure
Day 5
• 9:45am - departure
• Modica: 400-yr Sicilian chocolate- making tradition
• Clay workshop
• Ragusa
• 7:30pm - back to hotel
Day 6
• 8:45am - departure
• Taormina, “the Ionian Pearl,” for spectacular views of Mount Etna
• 1:30pm - back to hotel
• Special pizza dinner
Day 7
• 8:45am - departure
• Private sail boat to Grotto Azzurra & Isola Bella + a lunch onboard
• Local market visit + cooking class
• 9pm - back to hotel
Day 8
• 10:45am - departure
• Wine tasting + lunch
• 3pm - back to hotel for free time
• Farewell group dinner
Day 9 (Apr 20)
Departure day - any time
An In-Depth Look at Your Trip
Tastes of Palermo
A walking tour of Palermo's artistic & architectural landmarks
Indulge your senses in centuries-old culinary traditions, with Greek, Arab, Spanish and French influences
Visit the Ballarò Market & taste local specialties
Traditional dinner
Roman villa, artisanal crafts &
ceramics, & more!
Visit a Roman Villa at 721 meters above sea level, built in the middle of the 4th Century AD and home to some of the best preserved and extensive examples of Roman mosaics
Head to Caltagirone, well known for its ceramic art characterized by ornate traditional motifs using a limited palette.
The main highlight of the town is the 142 steps Staircase of Santa Maria del Monte, decorated with splendid glazed majolica tiles.
Ortigia city & food tour; street market, Sicilian wine & granita tasting
Explore Ortigia, the heart of the Syracuse city center
Cathedral built on the site of an ancient Temple of Athena
Colorful street market
A vintage delicatessen to taste typical Sicilian appetizers and local wines
Granita tasting at one of Siracusa’s renowned bars
Baroque, chocolate & pottery
Explore Modica’s 400 year tradition of Sicilian chocolate making
A short drive to Ragusa Ibla, one of the most picturesque towns in Sicily
One of the UNESCO-listed Baroque towns of south-eastern Sicily, Ragusa is also one of the principal filming locations for the Sicilian detective saga ‘Il Commissario Montalbano’
A 2-hour clay modeling workshop, guided and assisted by local artists - create a sculpture that will later be fired and sent home (extra shipping fee, not included).
Taormina & views of Mt. Etna
A cable car & a guided walking tour that visits the famous Greek-Roman Theatre
Leisure time to explore and do some shopping
A private sail boat to Grotto Azzurra & Isola Bella for a swim or snorkeling
With the backdrop of Taormina, enjoy a tasting lunch as we sail the pearl of the Mediterranean Sea.
Visit a local market with a chef; a cooking class and a 3-course lunch
"In every tour, in every class, in every meal prepared in my
restaurant, my goal is always the same, to teach my guests to learn to live like an Italian, to love like an Italian .. learn to BE Italian.”
Meet Your Host:
Chef Melina
Melina was born and raised in Australia by Italian immigrant
parents from Calabria, located in the south of Italy. At the age
of 19, she opened her first restaurant in Australia with her
brother, which was the beginning of her love affair with food.
At 22, Melina went to Italy for the first time and that's where
she left her heart. In 2009, Melina opened her cooking school,
traveling between both countries before transferring to Italy
indefinitely in 2017.
Melina began escorted food tours after realizing that the
story behind each dish, each plate is what it truly makes it
special. Her love for Italy, her love for food, and her passion for
sharing that is evident after spending just 5 minutes with her.
"Cooking is my biggest love but sharing
is my biggest joy."
Melina is the host of Olegana Travel Boutique’s women-only
group tours to Puglia and Sicily, where she happily shares her
love for Italy with other women.
What’s Included in Your Experience of a Lifetime
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Accommodations
8 nights at a hotelTour leader for the duration of the trip
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Tours & Activities
Per itinerary
Entry fees for all activities listed under Itinerary
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Food & Beverages
8 breakfasts, 4 lunches, and 6 dinners
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Transportation
Private group motorcoach/bus transportation to/from all activities unless stated otherwise
What Guests Said About Past Trips…
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“Anna and her team in Italy did a fantastic job in making sure we had an amazing time visiting Puglia. There were so many “out of the box” experiences that made this trip unique & wonderful.
The group of women brought together by Anna made the trip fantastic! Thank you for a memorable trip!"
- MJ
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“I can't say enough about Anna and Olegana Travel
Boutique!!! What an awesome trip first off, and the ladies I met OMG!!!She helped me plan an AMAZING and PERFECT itinerary.
This will not be my last trip with this Boutique.”
- Lucia
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“I went on the incredible Spain trip in the fall of 2023 and I was very impressed with the high quality of the tours, the guides and the accommodations.
Anna did a great job, and I wouldn’t hesitate to book another tour with her company."
- Lin
You Might Be Wondering…
Read through our frequently asked questions.
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Yes, only women (she/her) are welcome to join.
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All activities, food and beverages not listed under the itinerary
All items of a personal nature and anything not expressly stated as included
Airfare to/from your arrival city and departure city
Airport transfers in your departure city
Airport arrival and departure transfers - can be arranged at extra cost
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Insurance is strongly recommended. We can offer travel insurance for American travelers. Please let us know if you would like a quote for your travel insurance policy.
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Yes, a decent level of fitness is highly recommended. We’ll be walking a lot—think 10,000+ steps a day—often on uneven cobblestone streets, hilly paths, stairs with no railings, and all the charming, ancient terrain Italy is famous for. You don’t need to be a triathlete, but comfortable walking for extended periods is key.
If that sounds like too much, you’re welcome to enjoy a relaxing day at the hotel instead. We want you to have a beautiful, comfortable experience at your own pace.
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The group will meet at the hotel in Italy on April 12, 2026. Everyone will be responsible for purchasing their own plane tickets to get to Italy. We are happy to help find the best airfare options and plan a trip extension before or after the group trip. The traveler will be responsible for any extra costs associated with that.
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Each day in Sicily is designed to flow smoothly—whether we’re wandering seaside villages, heading to a pasta-making class, or watching the sun set over an active volcano (not a metaphor).
If you’d rather skip an activity and relax at the hotel, no problem—just let your tour host know well ahead of time.
To keep things on track and respect our local hosts, please be punctual. We’ll give friendly nudges, but the group won’t wait forever. And missing out on wine and chocolate in Sicily? That’s just tragic.
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Guide and driver pre-paid gratuities of $300 per person will be collected approximately a week before the trip starts.
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In Sicily, every bite tells a story—and we want you to savor all of it. Meals on this trip are carefully chosen in advance to highlight the best of the island’s culinary traditions, from bold reds and rich chocolates to fresh seafood, pistachio everything, and recipes passed down through generations.
We partner with local chefs and trusted restaurants to create a delicious experience that reflects the region’s vibrant food culture.
We ask guests to come with an open mind—and an adventurous appetite. Italian dining doesn’t always include the staples you might expect back home (you may not see a salad or breadbasket at every table), but what you will find is thoughtful, balanced food made with care, history, and flavor in every bite.
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We will provide a packing list closer to travel dates with suggested attire and useful gadgets. The trip is very casual, so as long as you are comfortable, you will be fine.
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No, this is an adults only group, for people 18 years old and older. If you’re under 50, don’t shy away - everyone is welcome! If you are interested in a family friendly adventure through Italy or any other country in Europe, we would be happy to create a custom trip for you. Please book a time on Anna's calendar here to discuss further.
Not sure if this trip is for you?
I hear it all the time - "I would love to come with you BUT..."
BUT I've never traveled alone!
This is a perfect option if you’re a solo traveler on a journey of self-discovery: you can be part of a larger group of women (usually 50+) that share your interests and have likely been in your shoes before, while going through a new stage of life like retirement, divorce or loss of a partner. Everyone is as excited to be on this trip as you are so you're not alone.
BUT I've never been to Europe!
That's ok - that's the beauty of travel and exploring new places! With our group, you don't have to worry about the logistics in an unfamiliar, new place. You're part of a small group that travels together with a professional, English-speaking guide and you get to know one another.
How amazing would you feel on the return flight home, knowing that you seized the chance to have a once-in-a-lifetime, authentic European experience and met some new friends along the way?
It’s time to feel that Italian sunset for yourself and learn all Italy has to offer!
P.S. This date doesn’t work for you? Check out our trips to Puglia in 2025 by clicking here.
See How Much Fun We Have!
Meet Anna
Hi - I’m Anna Fishman, the proud mastermind behind Olegana Travel Boutique, your go-to hub for unforgettable journeys.
I live for family adventures with my travel-loving husband and our little jetsetters in training. With 31 countries under my belt, I’ve combined my personal globetrotting escapades with the expertise of local destination gurus. Together, we craft personalized itineraries that are perfect for you to reconnect with your inner self, to discover the world, and to make new friends.
I can’t wait to meet you on our next group trip for incredible women!